HCID 86704551, compound → HCID 86704552, compound

HRID 633465Notes

Reaction equation

HRID 633465 reaction equation
[CH3:1][N:2]1[C:20](=[O:21])[N:5]2[C:6]3[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:7]=3[O:8][C:9]3([CH2:12][O:11][CH2:10]3)[C:4]2=[N:3]1>CO.[Pd]>[NH2:17][C:15]1[CH:14]=[CH:13][C:7]2[O:8][C:9]3([C:4]4[N:5]([C:20](=[O:21])[N:2]([CH3:1])[N:3]=4)[C:6]=2[CH:16]=1)[CH2:10][O:11][CH2:12]3

Participants

4

Reactant 1

HCID 86704551HCID 86704551, compound

Product 1

HCID 86704552HCID 86704552, compoundYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-8-nitrospiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazine-4,3′-oxetan]-1(2H)-one (150 mg) and 10% Pd—C were suspended in methanol (10 mL). The reaction mixture was shaken at room temperature under H2 atmosphere (30 psi) for one hour. The catalyst was filtered off over celite and washed with methanol (5×50 mL). The filtrate was evaporated to give 8-amino-2-methylspiro[benzo[b][1,2,4]triazolo[4,3-d][1,4]oxazine-4,3′-oxetan]-1(2H)-one (120 mg). m/z=261.16 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered off over celite
  2. washwashed with methanol (5×50 mL)
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-7f7c703310d841e7b7b5c637463bf79c
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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